I understand not being burdened by legacy but they are going too far, into not being burdened by users' needs.

I think there is not a single Apple notebook that was unable to drive a recent Apple or third party display, apart from the Thunderbolt display, which older units simply cannot (!) address.

All other connector changes are all still based around or on industry standards and mostly due to size constraints when building the notebooks as thin as we all like them.

Given the regular user buys a computer every couple generations, this is absolutely no biggie at all. And for the Thunderbolt display not working on older Macs because they don't have the feature: This is why Apple still sells the predecessor of the display.